Abstract:We report the palladium(II)-catalyzed aerobic oxidative coupling of isocyanides with various (2-aminophenyl)azoles using air as the stoichiometric oxidant. A diverse range of medicinally valuable azolo[c]quinazolines was obtained by this new approach.

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An efficient metal-free procedure for the formal α-carboxylation of primary alcohols has been developed. The method involves a one-pot oxidation/Passerini/hydrolysis sequence and provides access to α-hydroxy acids bearing a broad range of functional groups. A minor modification to the reaction conditions extends the range of accessible products to α-hydroxy esters.

Synthesis of Diverse Azolo[c]quinazolines by Palladium(II)-Catalyzed AerobicOxidative Insertion of Isocyanides. -The oxidative coupling of isocyanides with (2-aminophenyl)oxazoles using air as the oxidant provides azolo[c]quinazolines (III) and (V) with high selectivity. Only in some cases small amounts of regioisomeric products such as (VI) are obtained. Substrates bearing tetrazole or benzimidazole moiety react similarly under analogous reactions conditions. -(VLAAR, T.; BENSCH, L.; KRAAKMAN, J.; VANDE VELDE, C. M. L.; MAES*, B. U. W.; ORRU, R. V. A.; RUIJTER, E.; Adv. Synth. Catal. 356 (2014) 6, 1205-1209, http://dx.doi.org/10.1002/adsc.201301129 ; Dep. Chem. Pharm. Sci., Vrije Univ., NL-1081 HV Amsterdam, Neth.; Eng.) -Mais 37-183